WO2013175746A1 - 有機エレクトロルミネッセンス素子 - Google Patents

有機エレクトロルミネッセンス素子 Download PDF

Info

Publication number
WO2013175746A1
WO2013175746A1 PCT/JP2013/003147 JP2013003147W WO2013175746A1 WO 2013175746 A1 WO2013175746 A1 WO 2013175746A1 JP 2013003147 W JP2013003147 W JP 2013003147W WO 2013175746 A1 WO2013175746 A1 WO 2013175746A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
carbon atoms
formula
Prior art date
Application number
PCT/JP2013/003147
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
池田　剛
裕勝 伊藤
Original Assignee
出光興産株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 出光興産株式会社 filed Critical 出光興産株式会社
Publication of WO2013175746A1 publication Critical patent/WO2013175746A1/ja

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems

Definitions

  • the present invention relates to an organic electroluminescence element.
  • An organic electroluminescence (EL) element is a self-luminous element utilizing the principle that a light-emitting material emits light by recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied.
  • Organic EL elements have features such as low voltage drive, high brightness, diversity of emission wavelengths, high-speed response, and the ability to produce thin and light-emitting devices, and are therefore applied to a wide range of applications.
  • Organic compound materials used in organic EL elements have been actively studied since they have a great influence on the color of light emitted from the elements and the light emission lifetime.
  • Patent Document 1 discloses an anthracene compound with a four-ring condensed ring.
  • An object of the present invention is to provide an organic EL element with improved lifetime and luminous efficiency.
  • the present inventors When the organic light emitting layer containing a specific anthracene compound and the electron transport layer containing a specific azine compound are formed adjacent to each other, the present inventors have a long lifetime and high light emission efficiency. The inventors found that an element can be obtained and completed the present invention.
  • the following organic EL elements and the like are provided. 1. Between the anode and cathode facing each other, from the anode side, at least an organic light emitting layer and an electron transport layer are adjacent to each other in this order, The organic light emitting layer contains an anthracene compound represented by the following formula (1-1): The electron transport layer contains an azine compound represented by the following formula (2-1): Organic electroluminescence device.
  • Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 15 to 60 ring carbon atoms.
  • Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • L is a single bond or a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms.
  • R 1 to R 8 are each independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted An unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted ring An arylsilyl group having 8 to 50 carbon atoms formed.
  • n is an integer of 1 to 4, and when n is 2 or more, the plurality of L may be the same or different.
  • Ar 11 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms having at least one substituted or unsubstituted carbazole skeleton-containing group as a substituent.
  • Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group.
  • 2. The organic electroluminescence device according to 1, wherein the azine compound represented by the formula (2-1) has a substituted or unsubstituted carbazole skeleton-containing group which is a substituted or unsubstituted 9-carbazolyl group. 3. 2.
  • k is an integer of 1 to 3
  • n is an integer of 0 to 3
  • R 11 to R 18 are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms.
  • Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group.
  • the organic electroluminescence device according to 4 wherein Az in the formula (2-2) is a group represented by the following formula (2a).
  • X 1 to X 3 are each independently a nitrogen atom or CH, and at least two of X 1 to X 3 are nitrogen atoms.
  • Ar 12 and Ar 13 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms. ) 6).
  • Formula number of carbon atoms of Ar 12 in (2a) is equal to or less than the number of carbon atoms of Ar 13, the organic electroluminescence device according to 5 or 6. 8).
  • Ar 12 in the formula (2a) is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group. .
  • 9. The organic electroluminescence device according to any one of 4 to 8, wherein k in the formula (2-2) is 2. 10. 10.
  • the organic electroluminescence device according to any one of 4 to 9, wherein R 11 to R 18 in the formula (2-2) are hydrogen atoms. 11.
  • Ar 1 in the formula (1-1) is a substituent represented by the following formula (1a), (1b), (1c), (1d), (1e), (1f), (1g) or (1h)
  • one of R is a single bond bonded to L, and each R other than a single bond is independently a hydrogen atom, a fluorine atom, a cyano group, Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted ring formation A C6-C30 aryloxy group, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.) 13.
  • the organic EL device of the present invention has an organic light emitting layer and an electron transport layer adjacent to each other in this order between at least the anode side and the anode, and the organic light emitting layer has the following formula (1-1): And the electron transport layer contains an azine compound represented by the following formula (2-1).
  • azine is a 6-membered ring compound containing one or more nitrogen atoms in the ring.
  • Ar 1 is a substituted or unsubstituted aromatic hydrocarbon group having 15 to 60 ring carbon atoms.
  • Ar 2 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • L is a single bond or a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms.
  • R 1 to R 8 are each independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted Unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or substituted or unsubstituted And an arylsilyl group having 8 to 50 carbon atoms.
  • n is an integer of 1 to 4, and when n is 2 or more, the plurality of L may be the same or different.
  • Ar 11 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms having at least one substituted or unsubstituted carbazole skeleton-containing group as a substituent.
  • Az is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group.
  • a laminate comprising an organic light emitting layer containing an anthracene compound represented by formula (1-1) and an electron transport layer containing an azine compound represented by formula (2-1) is adjacent to each other.
  • the azine compound represented by the formula (2-1) is estimated to be able to smoothly inject electrons into the organic light emitting layer, and enables the device to be driven at a low voltage.
  • the charge balance can be optimized by including the anthracene compound represented by the formula (1-1) in the organic light emitting layer for smooth electron injection by the azine compound of the electron transport layer.
  • the organic EL element of this invention can show high efficiency and long lifetime.
  • the anthracene compound contained in the organic light-emitting layer is preferably such that Ar 1 in the formula (1-1) has the following formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g ) Or (1h), and more preferably any of the substituents represented by formula (1a), (1b), or (1h).
  • Ar 1 is any one of the groups represented by the following formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g) or (1h). And more preferably a substituent containing any of the groups represented by the formula (1a), (1b), or (1h).
  • the substituent containing a group represented by the formula (1a) or the like is preferably a group in which a group represented by the formula (1a) or the like is bonded to phenylene, naphthalenylene, biphenylene or the like.
  • a group represented by the formula (1a) or the like is bonded to phenylene, naphthalenylene, biphenylene or the like.
  • increasing the size of the condensed ring in the molecule increases the overlap between molecules and improves transportability.
  • the condensed ring is too large, the carrier balance may be lost and efficiency may not be obtained.
  • one of R is a single bond bonded to L, and each R other than a single bond is independently a hydrogen atom, a fluorine atom, a cyano group, substituted or unsubstituted.
  • a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms is there.
  • Ar 2 in Formula (1-1) is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group.
  • Ar 2 is one of these substituents, and it is considered that the carrier balance is more suitable when the device is manufactured and driven.
  • the biphenyl group in this application refers to any of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group.
  • L in Formula (1-1) is preferably a single bond or a substituted or unsubstituted phenylenyl group, and more preferably a single bond.
  • N is preferably 1.
  • L is a single bond, it is considered that a more suitable carrier balance is obtained when an element is formed and driven.
  • R 1 to R 8 in the formula (1-1) are preferably all hydrogen atoms. Since all of R 1 to R 8 of the anthracene ring are hydrogen atoms, the compound is considered to be stable, and is considered to have a long life when driven as an element.
  • Ar 11 of the azine compound represented by the formula (2-1) is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms and having one or more substituted or unsubstituted carbazole skeleton-containing groups as substituents.
  • the carbazole skeleton-containing group is preferably a carbazolyl group. Preferably it has 1 or 2 carbazolyl groups.
  • the substituted or unsubstituted carbazole skeleton-containing group for Ar 11 is preferably a substituted or unsubstituted 9-carbazolyl group.
  • the carbazole skeleton-containing group is preferably selected from any of the following. (Wherein L 100 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms, Ar 100 is a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. )
  • Az in the formula (2-1) is a substituted or unsubstituted aromatic nitrogen-containing 6-membered cyclic group, preferably a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, or a substituted or unsubstituted Triazinyl group.
  • Az in the formula (2-1) is preferably a group represented by the following formula (2a).
  • X 1 to X 3 are each independently a nitrogen atom or CH, and at least two of X 1 to X 3 are nitrogen atoms.
  • Ar 12 and Ar 13 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 (preferably 6 to 12) ring-forming carbon atoms. )
  • X 1 and X 2 are preferably nitrogen atoms, and X 3 is preferably CH.
  • the number of carbon atoms of Ar 12 in the formula (2a) is preferably less than or equal to the number of carbon atoms of Ar 13.
  • Ar 12 in formula (2a) is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group.
  • the azine compound represented by the formula (2-1) is preferably an azine compound represented by the following formula (2-2).
  • k is an integer of 1 to 3
  • n is an integer of 0 to 3
  • R 11 to R 18 are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms.
  • K in the formula (2-2) is preferably 2.
  • R 11 to R 18 in the formula (2-2) are preferably hydrogen atoms.
  • the “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring
  • the “ring-forming atom” includes a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring). ) Is a carbon atom and a hetero atom.
  • the hydrogen atom includes light hydrogen, deuterium, and tritium.
  • the aromatic hydrocarbon group preferably has 6 to 20 ring carbon atoms, and more preferably 6 to 12 ring carbon atoms.
  • Specific examples of the aromatic hydrocarbon group include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, benzoanthryl.
  • aromatic hydrocarbon group having a substituent include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group.
  • the aromatic heterocyclic group preferably has 5 to 20 ring atoms, and more preferably 5 to 14 ring atoms.
  • Specific examples of the aromatic heterocyclic group include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazol [ 1,2-a] pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, azadibenzothiophenyl group Quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group
  • alkyl group examples include linear, branched and cyclic alkyl groups.
  • the number of carbon atoms is preferably 1-20, and more preferably 1-10.
  • linear and branched alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl.
  • n-heptyl group, n-octyl group and the like preferably methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group and tert-butyl group. More preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, and t-butyl group.
  • cyclic alkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.
  • the alkoxy group is represented as —OY, and examples of Y include the above alkyl examples. Specific examples of the alkoxy group include a methoxy group and an ethoxy group.
  • the aryloxy group is represented by —OZ, and examples of Z include the above aryl groups. Specific examples of the aryloxy group include a phenoxy group and a naphthyloxy group.
  • the aralkyl group is represented by —Y—Z.
  • Y include alkylene examples corresponding to the above alkyl examples, and examples of Z include the above aryl examples.
  • the aryl part of the aralkyl group preferably has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms.
  • the alkyl moiety preferably has 1 to 10 carbon atoms, particularly preferably 1 to 6 carbon atoms.
  • benzyl group, phenylethyl group, 2-phenylpropan-2-yl group and the like can be mentioned.
  • haloalkyl group examples include groups in which one or more halogen atoms (a fluorine atom, a chlorine atom, and a bromine atom are preferable, and a fluorine atom is preferably substituted) on the alkyl group having 1 to 30 carbon atoms described above.
  • halogen atoms a fluorine atom, a chlorine atom, and a bromine atom are preferable, and a fluorine atom is preferably substituted
  • Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, and a pentafluoroethyl group.
  • they are a trifluoromethyl group and a pentafluoroethyl group.
  • haloalkoxy group examples include groups in which one or more halogens (including a fluorine atom, a chlorine atom and a bromine atom are preferable, and a fluorine atom is preferably substituted) on the above alkoxy group.
  • halogens including a fluorine atom, a chlorine atom and a bromine atom are preferable, and a fluorine atom is preferably substituted
  • it is a trifluoromethoxy group.
  • the alkylsilyl group is a silyl group substituted with 1 to 3 alkyl groups
  • the arylsilyl group is a silyl group substituted with 1 to 3 aryl groups.
  • the alkyl group and aryl group are the same as those described above.
  • the trialkylsilyl group is represented as —Si (R a ) (R b ) (R c ), and examples of (R a ), (R b ) and (R c ) include the alkyl groups described above. Specific examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, propyldimethylsilyl group and the like.
  • the dialkylarylsilyl group is represented as —Si (R a ) (R b ) (Ar c ), and examples of (R a ) and (R b ) include the alkyl groups described above, and examples of (Ar c ) Examples of the aryl group include the aryl groups described above. Specific examples include a phenyldimethylsilyl group.
  • the alkyldiarylsilyl group is represented as —Si (R a ) (Ar b ) (Ar c ), and examples of (R a ) include the alkyl groups described above.
  • Examples of the aryl group include the aryl groups described above. Specific examples include a methyldiphenylsilyl group.
  • the triarylsilyl group is represented as —Si (Ar a ) (Ar b ) (Ar c ), and examples of (Ar a ), (Ar b ) and (Ar c ) include the aryl groups described above. .
  • Specific examples include a triphenylsilyl group.
  • alkenyl group examples include vinyl, propenyl, butenyl, pentenyl, pentadienyl, hexenyl, hexadienyl, heptenyl, octenyl, octadienyl, 2-ethylhexenyl, decenyl and the like.
  • alkynyl group examples include ethynyl group and methylethynyl group.
  • the anthracene compound represented by the formula (1-1) can be synthesized by referring to, for example, WO2009 / 069566 and WO2011 / 054442.
  • the azine compound represented by the formula (2-1) can be synthesized by referring to, for example, WO2003 / 080760.
  • the content of the anthracene compound represented by the formula (1-1) in the organic light emitting layer adjacent to the electron transport layer is not particularly limited, but is, for example, 1 to 100% by weight, preferably 80 to 100% by weight, More preferably, it is 90 to 100% by weight.
  • the content of the azine compound represented by the formula (2-1) in the electron transport layer adjacent to the organic light emitting layer is not particularly limited, but is, for example, 1 to 100% by weight, preferably 50 to 100% by weight.
  • FIG. 1 is a schematic view showing a layer structure of an embodiment of the organic EL device of the present invention.
  • the organic EL element 1 the anode 20, the hole injection layer 30, the hole transport layer 40, the organic light emitting layer 50, the electron transport layer 60, the electron injection layer 70, and the cathode 80 are laminated on the substrate 10 in this order. It has a configuration.
  • the hole transport zone is a hole transport layer and a hole injection layer.
  • the electron transport zone is the electron transport layer 60 and the electron injection layer 70.
  • the hole injection layer 30 and the electron injection layer 70 do not have to be formed, but preferably one or more layers are formed respectively.
  • the organic light emitting layer 50 and the electron transport layer 60 are formed adjacent to each other.
  • the organic light emitting layer 50 is a layer containing the anthracene compound represented by the above formula (1-1), and the electron transport layer 60 contains the azine compound represented by the above formula (2-1). Is a layer.
  • FIG. 1 schematically shows the organic EL element 1 as one light emitting unit, but two or more organic EL elements 1 are combined, or the organic EL element 1 is combined with another organic EL element.
  • an organic EL multicolor light emitting device can be formed.
  • FIG. 2 is a schematic cross-sectional view showing an example of an organic EL light emitting device using the organic EL element of the present invention.
  • the organic EL light emitting device is a device having a blue EL element 1B (first element), a green EL element 1G (second element), and a red EL element 1R (third element) in parallel on a substrate 10.
  • the configuration of each color organic EL element uses patterned anodes 20B, 20G, and 20R, and the organic light emitting layer corresponds to each color, and the blue light emitting layer 50B, the green light emitting layer 50G, and the red light emitting layer 50R, respectively.
  • the organic EL element 1 is the same as that described above except that the hole injection layer 30 and the electron injection layer 70 are not formed.
  • the insulating layer 54 which isolate
  • the blue EL element 1B, the green EL element 1G, and the red EL element 1R share each organic layer (the hole transport layer 40 and the electron transport layer 60) except for the organic light emitting layer.
  • three colors of organic EL elements are used.
  • the present invention is not limited to this, and two (two colors) or four or more colors of organic EL elements may be used.
  • multicolor light emission is possible by setting the emission color of one organic EL element to blue to green and the emission color of the other organic EL elements to yellow to red. It becomes.
  • both the hole transport layer 40 and the electron transport layer 60 are formed as a common layer, either one may be used.
  • the organic EL element of this invention should just be used for one of the used organic EL elements.
  • Each EL element may be a fluorescent light emitting element or a phosphorescent light emitting element.
  • the organic EL element of the present invention is preferably used as the fluorescent blue EL element.
  • FIG. 3 is a schematic view showing the layer structure of another embodiment of the organic EL device of the present invention.
  • the organic EL element 2 is an example of a tandem organic EL element in which two light emitting units are stacked via a charge generation layer.
  • the organic EL element 2 includes an anode 20, a first hole transport layer 41, a first organic light emitting layer 51, a first electron transport layer 61, a charge generation layer 90, a second hole transport layer 42, a first hole on the substrate 10.
  • the second organic light-emitting layer 52, the third organic light-emitting layer 53, the second electron transport layer 62, and the cathode 80 are stacked in this order.
  • a region sandwiched between the anode 20 and the charge generation layer 90 is the first light emitting unit 3A
  • a region sandwiched between the charge generation layer 90 and the cathode 80 is the second light emitting unit 3B.
  • the charge generation layer 90 is a layer that generates charge when a voltage is applied to the organic EL element 2, and injects electrons into the first electron transport layer 61 and injects holes into the second hole transport layer 42.
  • a material of the charge generation layer 90 a known material, for example, a material described in US 7,358,661 can be used. Specifically, oxides, nitrides, iodides, borides containing one or more metal elements such as In, Sn, Zn, Ti, Zr, Hf, V, Mo, Cu, Ga, Sr, La, and Ru. Etc.
  • the first organic light emitting layer 51 of the first light emitting unit 3A is a layer containing the anthracene compound represented by the above formula (1-1), and the first electron transport layer 61 is the above-described layer. This is a layer containing an azine compound represented by the formula (2-1).
  • the first organic light emitting layer 51 is a fluorescent light emitting layer that emits blue light (for example, a peak wavelength is 430 to 500 nm), and the second organic light emitting layer 52 is green light (for example, a peak wavelength is 500 to 500 nm).
  • the third organic light-emitting layer 53 is a phosphorescent light-emitting layer that emits red light (for example, a peak wavelength of 570 nm or more), thereby obtaining an organic EL element that emits white light.
  • the present invention is not limited to this, and three or more light emitting units may be formed. Further, the second organic light emitting layer 52 and the third organic light emitting layer 53 may be combined to form a single layer.
  • the laminated structure peculiar to the present application is used for the first light emitting unit 3A. However, the present invention is not limited thereto, and for example, the laminated structure peculiar to the present application may be used for the second light emitting unit 3B. You may use for both unit 3A and the 2nd light emission unit 3B.
  • Each organic light emitting layer may be a fluorescent light emitting layer or a phosphorescent light emitting layer, and the emission color is not limited. What is necessary is just to set suitably according to a use from a well-known structure.
  • the organic EL element of the present invention can employ various known configurations.
  • light emission of the light emitting layer can be extracted from the anode side, the cathode side, or both sides.
  • organic EL element of the present invention other configurations of the organic light-emitting layer and the electron transport layer adjacent to the organic light-emitting layer are not particularly limited, and known materials and the like can be used.
  • the layer of the element of Embodiment 1 is demonstrated easily, the material applied to the organic EL element of this invention is not limited to the following.
  • a glass plate, a polymer plate or the like can be used as the substrate.
  • the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfone, and polysulfone.
  • the anode is made of, for example, a conductive material, and a conductive material having a work function larger than 4 eV is suitable.
  • the conductive material include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and their alloys, ITO substrate, tin oxide used for NESA substrate, indium oxide, and the like.
  • examples thereof include metal oxides and organic conductive resins such as polythiophene and polypyrrole.
  • the anode may be formed with a layer structure of two or more layers if necessary.
  • the cathode is made of, for example, a conductive material, and a conductive material having a work function smaller than 4 eV is suitable.
  • the conductive material include, but are not limited to, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and alloys thereof.
  • the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto.
  • the ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio.
  • the cathode may be formed with a layer structure of two or more layers, and the cathode can be produced by forming a thin film from the conductive material by a method such as vapor deposition or sputtering.
  • the transmittance of the cathode for light emission is preferably greater than 10%.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
  • Organic light emitting layer is not particularly limited as long as the organic light emitting layer adjacent to the electron transport layer contains an anthracene compound represented by the formula (1-1), and may be any of a known fluorescent light emitting layer and phosphorescent light emitting layer.
  • a fluorescent light-emitting layer is preferable, and an anthracene derivative is particularly preferable as a host material of the light-emitting layer.
  • the light emitting layer may be a double host (also referred to as host / cohost). Specifically, the carrier balance in the light emitting layer may be adjusted by combining an electron transporting host and a hole transporting host in the light emitting layer. Moreover, it is good also as a double dopant.
  • each dopant emits light by adding two or more dopant materials having a high quantum yield. For example, a yellow light emitting layer may be realized by co-evaporating a host, a red dopant, and a green dopant.
  • the light emitting layer may be a single layer or a laminated structure.
  • the recombination region can be concentrated on the light emitting layer interface by accumulating electrons and holes at the light emitting layer interface. This improves the quantum efficiency.
  • the hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a small ionization energy of usually 5.6 eV or less.
  • Examples of materials that can be used for the hole injection / transport layer include triazole derivatives (see US Pat. No. 3,112,197), oxadiazole derivatives (see US Pat. No. 3,189,447), imidazole, and the like. Derivatives (see Japanese Patent Publication No. 37-16096), polyarylalkane derivatives (US Pat. No. 3,615,402, US Pat. No. 3,820,989, US Pat. No.
  • a cross-linkable material can be used as the material of the hole injection / transport layer.
  • a cross-linkable hole injection / transport layer for example, Chem. Mater. 2008, 20, 413-422, Chem. Mater. Examples include a layer obtained by insolubilizing a cross-linking material such as 2011, 23 (3), 658-681, WO2008108430, WO2009102027, WO2009123269, WO2010016555, WO2010018813 by heat, light or the like.
  • the electron injection / transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a high electron mobility.
  • an electrode for example, a cathode
  • the electron injecting / transporting layer is appropriately selected with a film thickness of several nm to several ⁇ m.
  • the electron mobility is preferably at least 10 ⁇ 5 cm 2 / Vs or more when an electric field of V / cm is applied.
  • the electron transport layer adjacent to the organic light emitting layer contains an azine compound represented by the formula (2-1).
  • an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferable, and a nitrogen-containing ring derivative is particularly preferable.
  • the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
  • an organic layer having semiconductivity may be formed by doping (n) with a donor material and doping (p) with an acceptor material.
  • n doping
  • p doping
  • a typical example of N doping is to dope a metal such as Li or Cs to the material of the electron transport layer
  • P doping is to dope an acceptor material such as F4TCNQ to the material of the hole transport layer.
  • each layer of the organic EL device of the present invention a known method such as a dry film forming method such as vacuum deposition, sputtering, plasma, or ion plating, or a wet film forming method such as spin coating, dipping, or flow coating is applied. be able to.
  • the thickness of each layer is not particularly limited, but must be set to an appropriate thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
  • the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
  • the organic EL device of the present invention can be used in a panel module used for various displays as a light emitting device. Further, the panel module of the present invention can be used for a display device such as a television, a portable terminal, and a personal computer, lighting, and the like.
  • Example 1 A glass substrate with an ITO transparent electrode line of 25 mm ⁇ 75 mm ⁇ 1.1 mm (manufactured by Geomatic: ITO film thickness 130 nm) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and further UV (ultraviolet) ozone cleaning for 30 minutes.
  • the glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound HA is first deposited on the surface on which the transparent electrode line is formed so as to cover the transparent electrode.
  • a film was formed.
  • a compound HT1 was vapor-deposited on the HA film to form a 95 nm-thick hole transport layer.
  • the compound H100 which is a fluorescent host
  • the compound BD which is a fluorescent dopant
  • the compound ET100 was vapor-deposited on this fluorescent light emitting layer, and an electron transport layer having a thickness of 20 nm was formed.
  • the compound ET1 was vapor-deposited to form an electron injection layer having a thickness of 5 nm.
  • LiF with a thickness of 1 nm and metal Al with a thickness of 80 nm were sequentially laminated to form a cathode to manufacture an organic EL device. Note that LiF, which is an electron injecting electrode, was formed at a deposition rate of 1 ⁇ / min.
  • Example 2 An organic EL device is formed in the same manner as in Example 1 except that the hole transport layer is formed using the following compound HT2 instead of the compound HT1, and the electron transport layer is formed using the following compound ET200 instead of the compound ET100. did.
  • Example 3 An organic EL device was formed in the same manner as in Example 1 except that the compound ET200 was used instead of the compound ET100 to form the electron transport layer.
  • Example 4 A hole transport layer is formed using compound HT2 instead of compound HT1, a fluorescent light emitting layer is formed using compound H200 below instead of compound H100, and an electron transport layer is formed using compound ET200 instead of compound ET100.
  • An organic EL element was formed in the same manner as in Example 1 except that it was formed.
  • Example 5 An organic EL device was formed in the same manner as in Example 1 except that the fluorescent light emitting layer was formed using Compound H200 instead of Compound H100 and the electron transport layer was formed using Compound ET200 instead of Compound ET100.
  • Comparative Example 1 A hole transport layer is formed using compound HT2 instead of compound HT1, a fluorescent light emitting layer is formed using compound H300 below instead of compound H100, and an electron transport layer is formed using compound ET200 instead of compound ET100.
  • An organic EL element was formed in the same manner as in Example 1 except that it was formed.
  • the organic EL devices produced in the examples and comparative examples are made to emit light by direct current drive, and the luminance (L), chromaticity (x, y), luminous efficiency ⁇ (lm / W) at the current density of 10 mA / cm 2 , external Quantum efficiency (EQE:%) was measured. Further, the element lifetime (LT80) was measured. The results are shown in Table 1. The values of luminance, light emission efficiency ⁇ , external quantum efficiency (EQE), and element lifetime (LT80) in the table are relative values with the value of Comparative Example 1 being 100.
  • the organic EL element of the present invention has a long life and can be driven with high efficiency. Accordingly, it can be suitably used as a display device such as a television, a portable terminal, a personal computer, or a light emitting element such as an illumination.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/JP2013/003147 2012-05-22 2013-05-17 有機エレクトロルミネッセンス素子 WO2013175746A1 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2012116718 2012-05-22
JP2012-116718 2012-05-22

Publications (1)

Publication Number Publication Date
WO2013175746A1 true WO2013175746A1 (ja) 2013-11-28

Family

ID=49623457

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2013/003147 WO2013175746A1 (ja) 2012-05-22 2013-05-17 有機エレクトロルミネッセンス素子

Country Status (2)

Country Link
TW (1) TW201410840A (zh)
WO (1) WO2013175746A1 (zh)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160072077A1 (en) * 2014-09-04 2016-03-10 Samsung Display Co., Ltd. Organic light emitting diode and organic light emitting display device including the same
KR20160034804A (ko) * 2014-09-22 2016-03-30 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
WO2016117429A1 (ja) * 2015-01-20 2016-07-28 保土谷化学工業株式会社 ピリミジン誘導体および有機エレクトロルミネッセンス素子
JP2016540731A (ja) * 2014-06-27 2016-12-28 ヒソン・マテリアル・リミテッドＨｅｅｓｕｎｇ Ｍａｔｅｒｉａｌ Ｌｔｄ． 多環化合物およびこれを用いた有機発光素子
WO2017159152A1 (ja) 2016-03-15 2017-09-21 新日鉄住金化学株式会社 有機電界発光素子
WO2017179809A1 (ko) * 2016-04-11 2017-10-19 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
KR101832557B1 (ko) * 2015-04-09 2018-02-28 단국대학교 산학협력단 유기재료 및 이를 함유하는 유기발광다이오드
US10056558B2 (en) 2011-11-25 2018-08-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element
US10217954B2 (en) 2013-11-13 2019-02-26 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
CN111171010A (zh) * 2020-01-13 2020-05-19 北京大学深圳研究生院 一种阴极电刺激响应材料及其制备方法
US10784446B2 (en) 2014-11-28 2020-09-22 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescence element material, organic electroluminescence element and electronic device
CN112912359A (zh) * 2018-11-08 2021-06-04 出光兴产株式会社 新型化合物、使用其的有机电致发光元件和电子设备
KR102721427B1 (ko) * 2016-04-11 2024-10-25 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI691581B (zh) * 2019-01-11 2020-04-21 元智大學 含蒽材料、有機發光二極體元件以及含蒽材料製造方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010104184A1 (ja) * 2009-03-13 2010-09-16 三菱化学株式会社 有機電界発光素子の製造方法、有機電界発光素子、有機ｅｌディスプレイ及び有機ｅｌ照明
WO2010114243A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel compounds for organic electronic material and organic electronic device using the same
WO2010136109A1 (de) * 2009-05-29 2010-12-02 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
WO2011083588A1 (ja) * 2010-01-08 2011-07-14 三菱化学株式会社 有機ｅｌ素子及び有機発光デバイス
WO2011099374A1 (ja) * 2010-02-12 2011-08-18 新日鐵化学株式会社 有機電界発光素子
JP2012056880A (ja) * 2010-09-08 2012-03-22 Idemitsu Kosan Co Ltd インドロカルバゾール化合物、有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010104184A1 (ja) * 2009-03-13 2010-09-16 三菱化学株式会社 有機電界発光素子の製造方法、有機電界発光素子、有機ｅｌディスプレイ及び有機ｅｌ照明
WO2010114243A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel compounds for organic electronic material and organic electronic device using the same
WO2010136109A1 (de) * 2009-05-29 2010-12-02 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen
WO2011083588A1 (ja) * 2010-01-08 2011-07-14 三菱化学株式会社 有機ｅｌ素子及び有機発光デバイス
WO2011099374A1 (ja) * 2010-02-12 2011-08-18 新日鐵化学株式会社 有機電界発光素子
JP2012056880A (ja) * 2010-09-08 2012-03-22 Idemitsu Kosan Co Ltd インドロカルバゾール化合物、有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
US10056558B2 (en) 2011-11-25 2018-08-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element
US10217954B2 (en) 2013-11-13 2019-02-26 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
JP2016540731A (ja) * 2014-06-27 2016-12-28 ヒソン・マテリアル・リミテッドＨｅｅｓｕｎｇ Ｍａｔｅｒｉａｌ Ｌｔｄ． 多環化合物およびこれを用いた有機発光素子
US20160072077A1 (en) * 2014-09-04 2016-03-10 Samsung Display Co., Ltd. Organic light emitting diode and organic light emitting display device including the same
KR20160034804A (ko) * 2014-09-22 2016-03-30 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
KR101864473B1 (ko) * 2014-09-22 2018-06-04 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 발광 소자
US10784446B2 (en) 2014-11-28 2020-09-22 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescence element material, organic electroluminescence element and electronic device
CN107406415A (zh) * 2015-01-20 2017-11-28 保土谷化学工业株式会社 嘧啶衍生物和有机电致发光器件
JPWO2016117429A1 (ja) * 2015-01-20 2017-11-09 保土谷化学工業株式会社 ピリミジン誘導体および有機エレクトロルミネッセンス素子
US10566543B2 (en) 2015-01-20 2020-02-18 Hodogaya Chemical Co., Ltd. Pyrimidine derivative and organic electroluminescent devices
WO2016117429A1 (ja) * 2015-01-20 2016-07-28 保土谷化学工業株式会社 ピリミジン誘導体および有機エレクトロルミネッセンス素子
CN107406415B (zh) * 2015-01-20 2021-02-19 保土谷化学工业株式会社 嘧啶衍生物和有机电致发光器件
KR101832557B1 (ko) * 2015-04-09 2018-02-28 단국대학교 산학협력단 유기재료 및 이를 함유하는 유기발광다이오드
WO2017159152A1 (ja) 2016-03-15 2017-09-21 新日鉄住金化学株式会社 有機電界発光素子
US11088334B2 (en) 2016-03-15 2021-08-10 Nippon Steel Chemical & Material Co., Ltd. Organic electroluminescent element
WO2017179809A1 (ko) * 2016-04-11 2017-10-19 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102721427B1 (ko) * 2016-04-11 2024-10-25 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
CN112912359A (zh) * 2018-11-08 2021-06-04 出光兴产株式会社 新型化合物、使用其的有机电致发光元件和电子设备
CN111171010A (zh) * 2020-01-13 2020-05-19 北京大学深圳研究生院 一种阴极电刺激响应材料及其制备方法

Also Published As

Publication number Publication date
TW201410840A (zh) 2014-03-16

Similar Documents

Publication Publication Date Title
WO2013175747A1 (ja) 有機エレクトロルミネッセンス素子
JP6148982B2 (ja) 含窒素へテロ芳香族環化合物
WO2013175746A1 (ja) 有機エレクトロルミネッセンス素子
JP6047761B2 (ja) 有機ｅｌ多色発光装置
JP6310856B2 (ja) 有機ｅｌ多色発光装置
JP6012611B2 (ja) 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
WO2013035329A1 (ja) 有機エレクトロルミネッセンス素子
WO2012018120A1 (ja) モノアミン誘導体およびそれを用いる有機エレクトロルミネッセンス素子
WO2013105206A1 (ja) 有機エレクトロルミネッセンス素子用材料及びそれを用いた素子
JP6220341B2 (ja) ラダー化合物、及びそれを用いた有機エレクトロルミネッセンス素子
WO2013102992A1 (ja) 有機エレクトロルミネッセンス素子用材料とそれを用いた素子
KR20120052231A (ko) 함플루오렌 방향족 화합물, 유기 일렉트로루미네선스 소자용 재료 및 그것을 사용한 유기 일렉트로루미네선스 소자
US20150034927A1 (en) Material for organic electroluminescent element, and organic electroluminescent element using same
WO2007029806A1 (ja) アザフルオランテン骨格を有するアザ芳香族化合物及びそれを用いた有機エレクトロルミネッセンス素子
CN101321728A (zh) 具有咔唑基的二氨基亚芳基化合物及其用途
WO2013073169A1 (ja) 白色系有機エレクトロルミネッセンス素子
JP2013108015A (ja) 有機エレクトロルミネッセンス素子用材料
WO2013108589A1 (ja) 新規化合物、有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子
JP6031302B2 (ja) ヘテロ芳香族化合物及びそれを用いた有機エレクトロルミネッセンス素子
US9496508B2 (en) Material for organic electroluminescent element and organic electroluminescent element using same
WO2014112359A1 (ja) 有機エレクトロルミネッセンス素子

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13794546

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13794546

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP